A Chicago Girls’ Trip: The Ultimate Guide
Planning a Chicago girls’ trip? Lucky you! Chicago is a thriving metropolis that offers luxury hotels, high end spas, brunch spots galore and a thriving cocktail scene.
I recently went to Chicago with one of my blogger friends to check out everything it has to offer. Now, I’m sharing my top tips for where to eat, drink, play and stay during your Chicago girls’ trip. So, keep reading if you’re ready to take your Chicago girls’ trip itinerary to the next level.
Chicago is also an Instagrammer’s heaven. If you’re planning on taking photos for Instagram during your Chicago girls’ trip, you can check out my list of the best Instagram spots in Chicago here.
Note: This post was written in partnership with Thompson Chicago, Fairmont Chicago, Skydeck Chicago, First Lady Cruises, Aire Ancient Baths, Beatnik, Nico Osteria, Seoul Taco and Safehouse Chi. However, as always, all opinions are my own. This post contains affiliate links, meaning if you click a link and make a purchase, I will receive a commission at no additional cost to you.
Getting to Chicago
I’m based in New York City, so I hopped a direct flight to Chicago’s O’Hare Airport. O’Hare is a major airport hub in the U.S. so there are daily flights to Chicago from all over the U.S.
We took the train/subway followed by one bus to our first hotel, which cost a grand total of $5. It took us about an hour to reach the River North area from O’Hare.
We even had some friendly locals help us navigate the bus system. People in Chicago are just so darn nice.
Getting Around Chicago
We used a combination of the subway and buses to get around. Basic fare is $2.50 per ride.
Lyft and Uber also operate in Chicago although I’d stick to public as much as possible. It’s affordable, efficient and much cleaner than the NYC subway.
Where to Stay During Your Chicago Girls’ Trip
We were hosted by two fantastic properties in Chicago, both of which I can highly recommend.
Thompson Chicago
First up, we stayed at Thompson Chicago (21 E Bellevue Pl), a stylish luxury hotel in the River North Area. Our room was gorgeous, with floor to ceiling windows and a view of the lake and skyline, plush bed linens, and white robes for our use.
I’m not going to lie, the first thing I usually do when I stay at a luxury hotel is throw on a robe and grab a glass of champagne. Thompson Chicago was the perfect hotel for doing that 🙂
Thompson Chicago is perfect for a sophisticated girl’s getaway – I could definitely see hosting my birthday party or an upscale bachelorette party here. Every little detail is thoughtfully taken care of, and the hotel staff is incredibly nice and accommodating.
The location in River North means that you can easily walk to high end shopping, restaurants and bars, as well as Oak Street Beach and North Avenue Beach.
Fairmont Chicago
We then stayed at Fairmont Chicago. We stayed in a large suite overlooking Millennium Park and I was blown away by the view during our stay.
If you’re looking to explore the Millennium Park area and the other main tourists sites in the city, Fairmont Chicago’s location can’t be beat.
Plus, Fairmont Chicago is a great choice if you’re coming to Chicago if you want to splash out on a big suite so that you can enjoy some champagne as a group before hitting the town.
Things to Do During Your Chicago Girls’ Trip
Skydeck Chicago
Skydeck Chicago at Willis Tower (233 S. Wacker Dr.) is an absolute must-do in Chicago. It’s is the perfect place to catch a view of Chicago from 1353 feet up in the air – plus on a clear day you can also see Indiana, Wisconsin and Michigan in the distance.
Come right when they open if you want to enjoy your visit with fewer crowds. And don’t miss out on walking on its famous glass floor – if you dare!
Millennium Park
Millennium Park is Chicago’s most famous public space (201 E. Randolph St.). Located in the Loop neighborhood, Millennium Park is home to some of Chicago’s best public art, including the famous Cloud Gate installation. You might know it by its nickname: the Bean.
If you only have one day in Chicago, don’t miss out on exploring Millennium Park.
First Lady Cruises
Chicago has been known for its stunning architecture since the 1800s! In fact, Chicago was home to the world’s first skyscraper: the 10 stories high Home Insurance Building, which was built in 1885 and torn down in 1931.
The best way to explore Chicago’s architecture is by boat. We hopped on the Chicago’s First Lady Cruises Architecture Foundation Center River Cruise (112 E. Wacker Drive), which is the only river cruise partnered with the Chicago Architecture Center.
I’m going to be honest…I’m not an architecture buff so I was worried the tour would be boring. But, I had a blast. The docents do a great job of teaching you Chicago architecture for dummies in a way that’s fun and keeps you interested.
Aire Ancient Baths
If you’re ready to be pampered during your Chicago girls’ trip, Aire Ancient Baths (800 West Superior St.) is Chicago’s most luxurious spa to treat a birthday girl or a bride-to-be. And a great place to treat yourself.
I visit their NYC location with my husband for my birthday each year and I found the Chicago location to be even larger and more impressive of a space. If I could afford it, I would make Aire Ancient Baths a monthly…or even weekly…indulgence.
Picture a luxurious Roman bath but set in a candle lit restored factory from 1902. You can explore Aire Ancient Baths’ hot, warm and cold pools, two scented steam rooms, saltwater bath, and even get a massage.
Don’t forget to pack a swimsuit since the Aire Ancient Baths is a coed experience!
Garfield Park Conservatory
Garfield Park Conservatory (300 N. Central Park Avenue) contains beautiful botanical gardens that are perfect for a rainy or snowy day in the Windy City.
Make sure to check out the Desert House, which reminded me of Palm Springs, the Fern Room, which is a tropical paradise, and the Conservatory Horticulture Hall, which has a beautiful Moroccan tiled fountain.
Where to Eat in Chicago
Chicago is a total foodie town – portions are big, the pizza is deep and you can’t walk two steps without finding another restaurant you want to try. Here are my top resto picks for your Chicago girls’ trip.
Beatnik Chicago
Beatnik (1604 W. Chicago Ave) is one of Chicago’s most stylish and photogenic cafes. And the food and cocktails don’t disappoint. The menu features globally inspired small plates.
We went for dinner and loved the Baba Ghanoush and the Bone Marrow and Miso Scallops. My Chicago friends tell me that it’s also a great brunch spot.
Nico Osteria
Nico Osteria (1015 N Rush St) is an excellent Italian restaurant in the Thompson Chicago with a seafood focused menu. I’m really particular when it comes to Italian food and Nico Osteria totally delivered with its house-made Cacio e Pepe pasta and Charred Octopus.
We maaay have over-ordered, not realizing that Chicago portions are larger than NYC portions.
Giordano’s Pizza
Your Chicago trip won’t be completed until you sample some deep dish pizza. I shared an individual pie with a friend at Giordano’s (multiple locations; we visited 730 N. Rush St.), which was more than enough.
Deep dish pizza is a loooooooooot more rich than thin crust pizza. Honestly, they are totally different foods. Deep dish pizza is more like a cheese pie with less tomato sauce. No offense Chicago – I’m glad I tried deep dish pizza but I’m going to stick to my NYC thin crust slices.
Other popular spots to try Chicago deep dish pizza are Pizzeria Uno, which invented the deep dish pie in 1943, and Pequod’s Pizza. Both were recommended to us, but we were deep-dish-pizza’d out after visiting Giordano’s so didn’t check them out.
Wow Bao
Wow Bao (multiple locations; we visited 200 N. Michigan Ave.) isn’t just a place to get quick bao (hot steamed buns), potstickers and noodle bowls. It’s also an experience.
We ducked into Wow Bao to escape the rain and had no idea what we were in for, which made it so much for exciting. We placed our order at an automated kiosk and then our bao popped out in the cutest delivery window. How fun is that?
Seoul Taco
Seoul Taco (multiple locations; we visited 738 N. Clark Street) is a Korean Mexican fusion restaurant that’s a great spot for a quick and tasty lunch.
We tried and loved the Gogi Bowl, various tacos, Kimchee Fried Rice and a side of kinchee. I only wish I had enough room to also try the Gogi and Waffles!
Safehouse Chi
If you’re ready to get a little bit silly and aren’t too cool for school, Safehouse Chi (60 E. Ontario St.) is a fun spot for a bachelorette or birthday party. Especially if the bride-to-be or birthday girl loves James Bond or Austin Powers.
My favorite part of this spy themed restaurant was the exit. I’m not going to tell you why it’s so great, you’ll have to experience it for yourself!
Where to Caffeinate In Chicago
Chicago is full of great coffee shops and this short list doesn’t do it justice. But, here are a few great options.
Maison Marcel Coffee Window
The Maison Marcel coffee window is Chicago’s prettiest spot for coffee (2008 North Halsted – Armitage Street a block west of Halsted Street and down the side alley).
The cute outdoor coffee window and cafe is only open Thursdays to Sundays from 8 am to 6 pm, so plan your visit accordingly if you like your coffee with a side of stunning floral mural.
La Colombe Coffee Roasters
I dream of La Colombe’s draft lattes. They taste like you’re drinking a cloud! You can find addresses for their multiple Chicago locations here.
Petit Margaux
If you want to add a French twist to your Chicago girls’ weekend, Petit Margaux (11 E Walton St), located in the Waldorf Astoria Hotel, is a perfect spot for a cappuccino and one (or two…or three) French macarons.
Where to Imbibe During Your Chicago Girls’ Trip
Cindy’s Rooftop
Cindy’s Rooftop (12. S. Michigan Ave.), a bar/restaurant that’s practically a Chicago institution, boasts an iconic view of Millennium Park and Cloud Gate/The Bean from its patio.
Three Dots and a Dash
I’ll admit it. I’m obsessed with tiki bars. I love the kitsch factor – the wildly fruity drinks, the Polynesian themed cups and the bartenders in Hawaiian shirts. I can’t get enough of them.
Three Dots and a Dash (435 N. Clarke Street) is the best tiki bar I’ve ever visited – it feels upscale instead of cheesy and it has an impressive cocktail menu complete with flaming drinks. If you’re heading to Chicago for a bachelorette party, birthday party or just a regular ole girls’ weekend, this tiki bar is sure to impress your gal pals.
Lost Lake Tiki
Of course I visited another tiki bar in Chicago. I’m obsessed with them! Lost Lake Tiki (3154 W Diversey Ave) is the perfect place to grab a tropical cocktail in the hipster neighborhood of Logan Square.
My banana daiquiri came with a dolphin garnish made out of an entire banana!
If you’re trying to choose between Lost Lake Tiki and Three Dots and a Dash, Lost Lake Tiki is a bit more casual while Three Dots and a Dash is more glossy and refined. Although, why not just live a little and check out both?
Hampton Social
The Hampton Social (multiple locations we visited 353 W. Hubbart St.) is the perfect spot to sip a glass of frosé/frozen rosé underneath the Rosé All Day neon sign. That’s pretty meta, right?
If I Had a Few More Days…
I love museums, and I’m bummed that we ran out of time before I had a chance to visit The Art Institute of Chicago.
We saw Navy Pier from the water during our boat cruise, but I would have loved to head there for some fun and games.
I’d take a half day to visit one of Chicago’s beaches. Yes, they still count as beaches even if they are lakeside.
We walked around the residential area called Lincoln Park, but I’d steal an extra hour to explore the area’s namesake park, which has beautiful skyline views.
I love kitschy things, so I’d head to the ‘burbs to see Chicago’s version of the Leaning Tower of Pisa – the Leaning Tower of Niles (6300 W Touhy Ave, Niles, IL).
All in all, Chicago is a great choice for a girls’ weekend, whether you’re celebrating a birthday, bachelorette, or just want to spend some quality time with your gals.
Did I miss any of your fave Chicago spots? Let me know in the comments!
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